89684-58-2

Basic information

• Product Name: 1-(2,4-dihydroxy-3-nitrophenyl)ethanone
• Synonyms: 1-(2,4-dihydroxy-3-nitrophenyl)ethanone;12914-A1
• CAS NO: 89684-58-2
• Molecular Formula: C₈H₇NO₅
• Molecular Weight: 197.14488
• Mol File: 89684-58-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 102 °C
• Boiling Point: 273.8±35.0 °C(Predicted)
• Appearance: /
• Density: 1.520±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.19±0.20(Predicted)
• CAS DataBase Reference: 1-(2,4-dihydroxy-3-nitrophenyl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,4-dihydroxy-3-nitrophenyl)ethanone(89684-58-2)
• EPA Substance Registry System: 1-(2,4-dihydroxy-3-nitrophenyl)ethanone(89684-58-2)

Safety Data

• Hazardous Substances Data: 89684-58-2(Hazardous Substances Data)

Usage

Preparation

Resacetophenone by treatment with cerium (IV) ammonium nitrate in acetic acid at 50–60° yields 2,4-dihydroxy-3-nitro-acetophenone (good yield) (23%).

Upstream product

• 860505-24-4 5-acetyl-2,4-dihydroxy-3-nitro-benzoic acid 
• 64-19-7 acetic acid 
• 601-89-8 2-nitroresorcinol 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 108-24-7 acetic anhydride 

Downstream Products

• 101884-41-7 1-(2,4-dihydroxy-3-nitro-phenyl)-3t-[2]naphthyl-propenone 

Relevant articles and documents

SMYD2 INHIBITORS

The present disclosure generally relates to compounds having cellular anti-proliferative activities, and more particularly relates to compounds which inhibit the activity of human SMYD2, a SET and MYND domain-containing protein lysine methyltransferase.

Total synthesis of (-)-platensimycin by advancing oxocarbenium- and iminium-mediated catalytic methods

(-)-Platensimycin is a potent inhibitor of fatty acid synthase that holds promise in the treatment of metabolic disorders (e.g., diabetes and "fatty liver") and pathogenic infections (e.g., those caused by drug-resistant bacteria). Herein, we describe its total synthesis through a four-step preparation of the aromatic amine fragment and an improved stereocontrolled assembly of the ketolide fragment, (-)-platensic acid. Key synthetic advances include 1) a modified Lieben haloform reaction to directly convert an aryl methyl ketone into its methyl ester within 30 seconds, 2) an experimentally improved dialkylation protocol to form platensic acid, 3) a sterically controlled chemo- and diastereoselective organocatalytic conjugate reduction of a spiro-cyclized cyclohexadienone by using the trifluoroacetic acid salt of α-amino di-tert-butyl malonate, 4) a tetrabutylammonium fluoride promoted spiro-alkylative para dearomatization of a free phenol to assemble the cagelike ketolide core with the moderate leaving-group ability of an early tosylate intermediate, and 5) a bismuth(III)-catalyzed Friedel-Crafts cyclization of a free lactol, with LiClO4 as an additive to liberate a more active oxocarbenium perchlorate species and suppress the Lewis basicity of the sulfonyloxy group. The longest linear sequence is 21 steps with an overall yield of 3.8% from commercially available eugenol. Relay tactics: The stereocontrolled assembly of the potent antibiotic (-)-platensimycin in 21 steps and 3.8% yield from eugenol is described (see scheme; TBAF: tetrabutylammonium fluoride; Ts: toluene-4-sulfonyl). Highlights are 1) a rapid oxidative esterification of an acyl aromatic, 2) a reliable dialkylation protocol to form platensic acid, 3) a π-facial conjugate reduction of a dienone, 4) a TBAF-promoted alkylative dearomatization of a free phenol, and 5) a Friedel-Crafts closure of a free lactol.

AMINE DERIVATIVES AND THEIR USE IN BETA-2-ADRENORECEPTOR MEDIATED DISEASES

The present invention provides compounds of formula (I), wherein k, Ar, R2, R3, R4, R5, R4', R5', R6, R7, A, D, m and E are as defined in the specification, processes